JPS60146864A - Amine and alkali metal double salt of acylamidoalkylene ( or acylamido-n-hydroxyalkyl-n-alkylene)sulfosuccinic acid,manufacture and use - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to surfactants, and more particularly to novel compounds, namely acylamidoalkylene (or acylamido-N-hydroxyalkyl-N-alkylene)-sulfosuccinic acid amines and alkali metal complexes. The present invention relates to salts, methods for producing the same compounds, and their use as cleaning agents.

These compounds are found in household chemicals, especially cosmetic preparations,
useful as anionic surfactants for the production of hair washes, bath lathering solvents, toilet soaps, stabilizers for cosmetic preparations, as well as in compositions for washing car heads, especially wool products in cold water; It is useful as a wetting agent in the application of emulsions to film in the manufacture of motion picture and photographic materials.

Modern cosmetic surfactants have high cell number and foam stability in aqueous solutions, good solubility in cold and hot hard water, mild dermatological effects and mild degreasing effects,
and must have increased biodegradability.

Known in the art are surfactants such as the disodium salt of acylamidoethylene sulfosuccinic acid produced from the cotton saw slag of oil extraction plants (Uzb
ek Ohemiaal Journal, Uzb.

SSRAcademy of Scienoeg, N
o, 3+pp, 52-54°1975).

It has the following general formula: That is, R-0-N
H-OH* -OH* -0-0-0H-CHt -C
OONa0sNa where R is a straight chain hydrocarbon group at ctt.

However, these substances have insufficient solubility in cold water and it is only possible to prepare pasty cleaning compositions from them which are not very suitable for cleaning in cold water.

Coconut oil, palm oil and other vegetable oils (FRB Patent No. 2)
,408. j395) and synthetic fatty acids (Uzb
ek Chamioal Journal, No, 3*
pp, 52-54t19T5) are also known.

The use of some vegetable oils, synthetic fatty acids, and animal fats as raw materials that contain saturated carbon chains with more than 13 carbon atoms results in limited cold water solubility and surface-active properties. Low surfactant is produced. Surfactants produced from such raw materials are not very suitable for cosmetic applications. Surfactants of this type produced from fatty acids with a large number of carbon atoms up to 14 have an excessive degreasing effect.

The surfactants according to the invention are new and not yet known in the literature.

The novel substance according to the invention, namely acylamidoalkylene (or acylamido-N-hydroxyalkyl-
The amine and alkali metal double salts of N-alkylene)sulfosuccinic acid have the following general formula. That is, where R, is a straight chain hydrocarbon group Rsu hydrogen CHt, -CHt-GHs, -CHt-CHt of Cl-011
-OH; R4・R, ・R4 are each hydrogen and/or -
Oh.

-CH, -OH and Me are Na or K.

The new compound according to the invention contains a dough-like substance that is completely soluble in cold water (a 40% solution is clear and has good flow properties at a temperature of 20 °C, and when stored Does not become cloudy). This compound is characterized by good heat resistance, additionally has a mild dermatological effect and is easily biodegradable.

The structure of the compounds according to the invention is determined by infrared spectroscopy. The spectrum has the following characteristic absorption bands of the functional groups. That is, alkyl group -725-720an'; C3H,-,
OH, - group 2.960; 2,940-2,910;
2.87 (to) ",'; -Co-NH- group 3,35
0-3.300: 3,05G-3,010cm'
;I+ -C-〇- group 1,750-1.735an'';-CO
, Io/1+61F1+550; 1,450-1,
300crn';-CH group 3,500-3,250
; 1,050-1,030 (!1+” ;-80,
-0- group 1.420-1.330; 1,200-1
,145 an” NH4-ioy 3e300-
3,030 an'.

The presence of anionic double charges in the compounds according to the invention is demonstrated by the method of cation exchange in aqueous alcohol solutions.

The density of aqueous solutions of these compounds at concentrations ranging from 24 to 32% by volume is 1.062 to 1,1o2 at a temperature of 20 °C.
kg/r+? The dynamic viscosity of these solutions at a temperature of 20 °C is in the range of 20-34 mPa5. is within the range of

The new compounds according to the invention exhibit surface-active properties.

The number of ponds of these substances determined by the Ross-Miles method at a temperature of 40°C and a concentration of 0.25% by volume is 180-196.
Characterized by the initial height of oil column in distilled water, its foam stability H,/H1 is 0.98-0.98. 5.35
■ In hard water with a concentration of calcium and magnesium salts of - equima/g, the initial height of the oil column is 1
The foam stability is 0.96 to 97.

The cleaning test of the novel compounds according to the invention was judged according to the standard Fisherman IK (FJ, Nevolin “Chemi
stryandteology of 8yn
thetioDetargents”.

Pisohevaya Promyghlennost
' (Food Zndustry) Publish
rs, Mogoow, 1971. pp, 405-4
15).

At a concentration of these compounds of 0.25% by volume, the cleaning efficiency is in the range of 90-96.

The surface tension of an aqueous solution of the compound according to the invention is determined at a temperature of 20°C.
, determined by thermometry at a concentration of 0.1% by volume in an aqueous solution. This is 28.1~31.6 X I F'Mum
was within the range.

The method for producing the new compounds according to the invention is as follows. That is, the acid value is 50 mg KOH/g or less, the saponification value is 181 to 192 KOH/g, and the bromine value is 60 to 70.
A fat-containing effluent from a seafood processing plant containing 7100 g of Br of fatty acids and glycerides is treated with methanol in the presence of sulfuric acid when heated at reflux to form a reaction mixture from which a fat layer consisting of glycerides and fatty acid methyl esters is extracted. Separation and treatment with methanol in the presence of sulfuric acid at a temperature of 50-60°C to produce a reactant, from which the anhydrous fat layer is separated and treated with methanol in the presence of an alkali at the boiling temperature of methanol to obtain methyl fatty acids. A reaction mixture containing the ester is formed, the fatty acid methyl ester is separated and the fatty dimethyl ester is separated in the presence of a catalyst selected from the group consisting of an alkali metal or its amide or alcoholade at a temperature in the range of 10 to 90°C. The fatty acid alkylolamide was treated with 25-55% by volume of the alkylolamine taken in the amount of After producing the maleate salt of fatty acid alkylolamide, the maleate salt is treated with sodium pyrosulfite or potassium pyrosulfite i and ethanolamine or ammonia in an aqueous medium at a temperature of 60 to 90°C to produce the desired product. Separate things.

In order to improve the quality of the desired product, the fatty acid methyl esters are treated at a temperature of 70 to 80° C. in the presence of the catalyst and before the above treatment with the alkylolamine. After pretreatment with an alkylolamine taken in an amount of 1% by volume, the waste alkylolamine is removed.

As the alkylolamine, it is preferable to use ditanolamine, diethanolamine, diisopropanolamine, N-methylethanolamine, K-ethylethanolamine, diptanolamine.

In order to simplify the procedure at the stage of amination of fatty acid methyl esters, it is preferred to use sodium 2-aminoethoxylade as catalyst.

Preferably, monoethanolamine, diethanolamine and/or triethanolamine are used as ethanolamine.

The process according to the invention is carried out in the following manner.

Acid value: 5 G mg KOH/g or less, saponification value: 181-1
92mg ICOH7g, Brominated 60-70 rr@
Fat-containing waste in the form of effluent from a seafood processing plant containing Br/100 g of fatty acids and glycerides is treated with methanol in the presence of sulfuric acid as catalyst.

Due to this K, free fatty acids contained in the fatty waste substances of the waste liquid are converted into acidic esters. The esterification reaction is carried out by stirring the reaction mixture for 1.5 to 2.5 hours at the boiling temperature of methanol. When the reaction is complete, the mixture is allowed to settle and the upper layer (methanol) is separated and recycled to regeneration, while the lower layer, the fat-containing mixture, is treated with methanol in the presence of sulfuric acid at a temperature in the range of 50-60°C. During precipitation, the upper layer (extracted methanol) is separated and recycled to an earlier stage of the cycle to acidify the free fatty acids of the effluent fatty waste. The bottom layer, the clarified fat mixture, is sent to alkaline re-esterification of glycerides.

For this purpose, the clarified fat mixture is treated with methanol in the presence of an alkali. The mixture was stirred at the boiling temperature of methanol for 0.25 hours, then cooled to room temperature for 1.5-2 hours.
Let settle for 0 hours and separate the layers. lower layer i.e. guri-74-
and methanol are sent to methanol regeneration. The upper layer of fatty acid methyl ester is washed with hot water acidified with hydrochloric acid and dried. Methanol is regenerated from the wash water. 155 at a vacuum of 10-20 mHg for dry methyl ester.
Fractional vacuum distillation is carried out at a temperature within the range of ~215°C.

The yield of the desired fraction is 18-83% of the initial amount of fat in the fat-containing waste of the effluent. Purified fatty acid methyl esters are treated with alkylolamines collected in an amount of 25-55% by volume of the amount of fatty acid methyl esters at a temperature of 70-90°C in the presence of a catalyst such as an alkali metal, its amide or lard. Geography.

Fatty acid alkylolamide is thus produced.

To simplify the process, sodium 2-
Use aminoethoxylates.

As alkylolamines, monoethanolamine, jetanolamine, diisopropanolamine, N-methylethanol, N-ethylethanolamine are used.

In order to improve the quality of the desired product, the fatty acid methyl esters are treated at a temperature in the range of 70-80° C. by 50% of the amount of fatty acid methyl esters before the above-mentioned treatment with the alkylolamine in the presence of the catalyst. After pretreatment with alkylolamine taken in an amount of ~10% by volume, the waste alkylolamine is removed by settling.

The yield of fatty acid alkylolamide, calculated on the degree of conversion of the alkylolamine, is 93-98% of the theoretical value.

The resulting alkylolamide was heated at a temperature of 60-90°C 1.
30-31% by volume of alkylolamide for 5-3.5 hours
of maleic anhydride. The yield calculated for the degree of conversion of maleic anhydride is close to the theoretical value.

The maleic acid alkylolamide thus produced is
Treatment with sodium or potassium pyrosulfite and ethanolamine or ammonia in an aqueous medium at a temperature in the range from 60 to 90[deg.] C. produces the desired product. The yield of the desired product is 70% of the initial alkylolamide.
~82%.

The process according to the invention makes full use of waste soda sludge originating from fisheries-processing plants, thus replacing the expensive food-grade fats and oils as well as synthetic petroleum-based feedstocks currently used in the production of surfactants. It becomes possible to replace it. It also contributes to reducing environmental pollution.

This method is technically simple and does not require any special equipment. The waste soda slag used in the process according to the invention has hitherto not been used in fine organic synthesis because of its excessive contamination. For the above-mentioned work, the method according to the invention provides high-quality objects that serve as a basis for the production of cleaning agents without the use of special additives in order to enhance the dermatological and cleaning effects from these raw materials. It becomes possible to generate products. The invention also encompasses the use of the novel compounds as bases for cleaning compositions. Preference is given to using the double triethanolamine and sodium salt of azilamidoethylene-sulfosuccinic acid.

The cleaning composition according to the invention, which contains a surfactant, a fragrance and water, contains as a surfactant the ditriethanolamine and sodium salt of azila ζ-doethylenesulfosuccinic acid of the following general formula: ing. That is, 0 0 R-C-NH-OHl -OH* -0-0-OHt
-CM-00ONH((:j s H40H)s80,
Na However, R is a linear hydrocarbon consisting of OII-CII, and the component ratio (volume %) is as follows. That is, triethanolamine and sodium double salt of acylamide ethylene sulfosuccinic acid 50-32.0 Fragrance 0.1-1.5 Water Balance Preferred embodiments of the cleaning composition according to the present invention further include the following: This is a composition containing CI-ctt fatty acid jetanolamide, sodium chloride, and ethanol in component ratio (volume %). That is, triethanolamine and sodium double salt of acylamide ethylene sulfosuccinic acid 12.0-20. OC*-C*V fatty acid jetanolamide 0.5-3
．． 5 Sodium chloride 1.0-3.5 Ethanol 0.3-1.5 Fragrance 0.1-1.5 Water Balance The cleaning composition according to the present invention has the following properties compared to known compositions:
It does not require the use of additives that reduce the degreasing effect.

It also has good solubility in cold and hot hard water and a high number of ponds, making it easy to wash away.

Furthermore, the cleansing composition according to the invention has mild dermatological properties and can be easily biodegraded.

In order to better understand the invention, some specific examples are presented below.

Example 1 500ml flask with reflux condenser and thermometer=t
J/C1 Fat waste generated from factories in the seafood processing industry (acid value 24 ■KOH/g, saponification value 181 ■KOH/g, bromine value 66.21f1g Br/100g, density smoked =
0.914ki,/rl.

solidification temperature 13.8℃) 250 g, and 1.3 g (
63 g of methanol acidified with 0.0125 g-mol) of concentrated sulfuric acid are introduced. The mixture is heated at reflux for 1.5 hours, resulting in esterification of the fatty acids. The reaction mixture was allowed to settle for 0.25 hours, the upper layer (methanolic) was separated,
The lower layer consisting of glycerides and fatty acid methyl esters was added at a temperature of 58 to 60°C.
ol) with 47.5 g of methanol acidified with concentrated sulfuric acid. After settling for 0.25 hours, separate the layers.

The upper layer (extracted methanol) is recycled to the initial stages of fatty acid esterification.

The lower layer (245 g) was placed in a 500 ml flask equipped with a reflux condenser, stirrer and thermometer, and 35.6 g (1,
1.61 (0, 113 g-mol) in methanol
Add 0.415 g/mol of caustic soda. The mixture was stirred at the boiling temperature of methanol for 0.25 hours.

An alkaline re-esterification of the glycerides takes place, after which the reactants are cooled to a temperature of 20.degree. Reaction mixture to 0
．． After settling for 5 hours, the glycerol-methanol layer (lower layer) is separated. The upper layer, namely fatty acid methyl ester, was washed with water acidified with hydrochloric acid (0.43% by volume),
Three fractions are collected by distillation at a temperature within the range of 155-215°C (15 Dragon Hg).

Fraction 1155-193℃ (Acid value 2.51 ■KOH/g
.

Saponification value 1s z xoH/g, bromine number 52 mg Br
/100g.

Density aS@=o, a r akg/n? , freezing point 30℃
, average molecular weight 290.0) Fraction n: 193-202°C (acid value 1.s r mg
KOH/gχ saponification value 189 mg KOH/g, bromine value T 1 n@Br/100g.

Density a4=s r okg/m”, freezing point -9.3°C,
Average molecular weight 295.0) Fraction 1: 202-215°C (Acid value 1.32 n@KO
H/g.

Saponification value 186 mg KOH 7g, bromine value 68 mg
Br/100g.

Density a4=o, aerkg/n? , freezing point 15.2℃,
295 g (1,00 g-mol) O-distilled fatty acid methyl ester (fraction ■) and 30 g monoethanolamine (0,491 g-mol) were added to a 500 ml flask equipped with a stirrer, a distillation apparatus, and a thermometer. mol). The mixture was stirred at a temperature of 70-72 °C for 0.25-0.3 hours, after which the stirrer was stopped and after settling 0.25-0.3
Remove the darkened underlayer of monoethanolamine with a pipette within an hour.

80 g (1,310 g-mol) of no-v-no-tanolamine were placed in the flask, the mixture was stirred at a temperature of 80° C. and then the catalyst, i.e., sodium 2-aminoethoxylate, in a 37.8% monoethanolamine solution was added.6.
Add 8g. Reaction time is 1.2 hours. 200
The mixture is heated to a temperature of 90° C. under reduced pressure of mmHg and the methanol is distilled off. Excess monoethanolamine is removed by distillation under reduced pressure of 20 to 25 mn+Hg at an internal temperature of 125° C. or lower in the reaction flask. Thus 328 g of fatty acid monoethanolamide with an average molecular weight of 324
is obtained. The product yield, calculated on the degree of conversion of monoethanolamine, is 96% of theory.

324 g of the resulting fatty acid monoethanolamide was placed in a 1,000 ml flask equipped with a thermometer and a stirrer.
Heat to a temperature of 1°C and stir for 0.25-05 hours.
08 g (1.1 g −1 nol) of maleic anhydride are added. The mixture was stirred for 15 hours under these conditions to yield 432 g of acidic oleic acid monoethanolamide (
Maleic acid acylamide ethylene) is produced.

2,000 m1 equipped with thermometer, stirrer and addition funnel
In a flask, add 956 ml of water. Sodium pyrosulfite 12
2 g (0,642 g-mol) and equivalent weight 127
A solution is prepared from 163 g (1,284 g-mol) of a mixture of jetanolamine and triethanolamine. The solution is heated to a temperature of 60 DEG C. and at this temperature for 0.3 to 0.5 hours the resulting acidic maleic acid monoethanolamide is added for sulfidation and neutralization.

Stirring is continued for 0.3 to 0.5 hours to produce 1,670 g of the desired product, an aqueous solution of triethanolamine and sodium double salt of acylamidoethylene sulfosuccinic acid having the following general formula. That is, SO, Na where R is 0n-a, and the content of the target product is 3
It is 1.2% by volume. Average molecular weight of the product is 650, total solids 40.2%, degree of conversion (desired product/initial amide) 82.0%, QOI solubility in a 4.5X, 2
Viscosity at 0℃ 32.011P&lL Density 441.098
kg/rrl, pH (10% solution) 6.85.

Example 2 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1 above.

295 g (1,0 Og-mol) of distilled fatty acid methyl ester (distillate...), 30 g (0,285 g
-mol) of jetanolamine and further processing is carried out as described in Example 1. Next, 110 g of jetanolamine (1,05
g-mol) and Natriu A2-7 minoethoxylate in a 31.8% monoethanolamine solution 7.3
Add g. The mixture is stirred at a temperature of 70°C to obtain a homogeneous solution. The reaction time is 2 hours. 200mmHg
The mixture is heated to 90° C. under reduced pressure and the methanol is distilled off to produce 383 g of fatty acid jetanolamide with an average molecular weight of 369. The product yield calculated based on the degree of conversion of jetanolamine was 8T% of the theoretical value.

383 g of the resulting jetanolamide was placed in a 500 ml flask equipped with a stirrer and a thermometer and the mixture was heated to 60°C.
142 g (1.45 g-mol) of maleic anhydride are added in portions for 0.5 hours. 65% solution
Stir for 3.5 hours at a temperature of °C and leave at room temperature for 12 hours.

Thus, 525 g of acidic maleic acid jetanolamide (maleic acylamide-N-hydroxyethyl-N
-ethyl) is obtained.

2,00 (1 m
1 flask, 918 ml of water. Sodium pyrosulfite 1515 g (0,834 g-mol) and equivalent weight 120
A solution was prepared from 199.2 g (1,661-mol) of a mixture of jetanolamine and triethanolamine and heated to a temperature of 80 °C to give 0.3-0.
．． Add the acidic maleic diethanolamide prepared above via the addition funnel while stirring for 5 hours. Continue stirring for 0.3-0.5 hours.

There is thus obtained 1,800 g of an aqueous solution of the triethanolamine and sodium double salt of the desired product, acylamido-hydroxyethyl-doethylenesulfosuccinic acid of the general formula: That is, CH*0HtOHSO*Na, where R is G II - CII, and the content of the target product is 2T volume %. Average molecular weight of the product is 695, total solids 46.3%, degree of conversion (desired product/initial amide)
r o, o%, (solubility in 3C1a 6.5%, 20
Viscosity at °C 28 mPag, severity a41. oa
skg/rI! , pH (10% solution) S, SO.

Example 3 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1 above.

Into a 500 ml flask equipped with a stirrer, distillation apparatus and thermometer was added 133 g of diisopropanolamine (1,00
g-mol), Natriu A2-7mi/,? - Add 7.5 g of a 3768% monoethanolamine solution of toxylate.

295 g (1,00 g-m0) of distilled fatty acid methyl ester (Fraction 11) pretreated with diisopropanolamine
Add 1) to a flask and stir at 80-82°C for 2 hours. The mixture is heated to a temperature of 90° C. under reduced pressure of 200 mmHg and the methanol is distilled off. In this way, 400 g of fatty acid diisopropanolamide having an average molecular weight of 396 is obtained. The product yield, calculated on the degree of conversion of diisopropanolamine, is 92% of theory.

To the resulting diisopropanolamide (396 g), add 127 g (1,3 g-mol) of maleic anhydride at a temperature of 60° C. and maintain this temperature for 2.51 hours. -N-2-hydroxypropyl-li-propylene)5
Produces 23g. Sulfurization and neutralization of acidic acid salt tetrapanolamide is carried out with water 1,
440ml s Sodium pyrosulfite 140g (0,
736 g-mol) and triethanolamine 219
In a similar manner to that described in Example 1 above, the acylamide -N-2- of the formula: 2,290 g of an aqueous solution of triethanolamine and sodium double salt of hydroxypropyl-N-propylene sulfosuccinic acid are produced. That is, Cl*
-0H-OH80* Na am where R is 0B-C1h Content of target product is 24.6
It is capacity %.

Average molecular weight of the product is 14T1 total solids 34.7%, degree of conversion (desired product/initial amide') 75.6%, C
Solubility in 014: 6.8%, viscosity at 20°C: 16.0s
eas 0, density (1,1,082kg/rr1.p
H (10% solution) is 6.82.

Example 4 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1.

110 g of K-methylethanolamine (1,4
65 g-mol), a 37.8% monoethanolamine solution of sodium aminoethoxylate yo, g, and 265 g of distilled fatty acid methyl ester (Fraction II) pretreated with N-methylethanolamine (0,898
g - mol ) and the mixture is stirred for 1.5 hours at a temperature of 80-83 °C. Then at a temperature of 90°C 200
Methanol is distilled off under reduced pressure of mmHH. Extra 1 methyl ethanol ty is 10-15 mmHg
The average molecular weight is 3 by distillation at a temperature of 120-123℃.
307 g of 38 fatty acid H-methylethanolamide are produced.

The product yield calculated for the degree of conversion of K-methylethanolamine is equal to the theoretical value of 115XK. To the resulting fatty acids - 306 g of methylethanolamide, 110 g (1
, 1221-mol) of maleic anhydride was added at a temperature of 65°C and stirred at this temperature for 2 hours to form acidic maleic acid N.
-Methylethanolamide (maleic acylamide-
416 g of N-methyl-ethylene) are produced.

Sulfidation and neutralization of acidic acid H-methylethanolamide was carried out using 1,356 ml of water, 107 g (0,563 g-m01) of sodium pyrosulfite and 168 g (1,122 g-m01) of triethanolamine at a temperature of 70 °C.
1) in a similar manner to that described in Example 1, by adding it into a solution containing K.
2.045 g of an aqueous solution of triethanolamine and sodium double salt of acylamido-N-methyl-N-ethylenesulfosuccinic acid of the formula below are produced. That is, where R is c 11 ”-a ts, and the content of the target product is 27.6% by volume. The average molecular weight of the product is 689
, total solids 31.5%, degree of conversion (desired product/initial amide) 82.0%, solubility in Gel 5.7%,
Viscosity at 20°C 34. ' OmPa5. , density a41
．． o 94 kg/rrl.

pH (10N solution) is 6.96.

Example 5 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1.

290 g of distilled fatty acid methyl varnish (distillate ■) in a 500 ml flask equipped with a stirrer, distillation device and thermometer.
(1,0Og-mol), mo/z// -y7miy29
g (0,475 g-mol) and the post-sono treatment was carried out as in Example 1 above.

In the next step, monoethanolamine y7 is converted to fatty acid methyl ester.
2.5 g (1,187 g-mol) and sodium 2
- Add 48 g of a 31.8% solution of aminoethoxylate in monoethanolamine. The temperature is increased to 90°C and stirring at this temperature is continued for 1.2 hours.

Methanol and excess monoethanolamine are removed in a manner similar to that of Example 1 to produce 322 g of fatty acid monoethanolamide with an average molecular weight of 319. The product yield, calculated on the degree of conversion of monoethanolamine, is 96% of theory.

319 g of fatty acid monoethanolamide thus produced
Add 102 g (1,04 g-mol) of maleic anhydride at a temperature of 80°C and stir at this temperature for 1.5 hours to produce 421 g + 74 maleic acid monoethanolamide (maleic acylamide ethylene). .

Sulfidation and neutralization of the acidic maleic acid monoethanolamide was carried out in 630 ml of water at a temperature of 70°C. In a solution containing 114 g (0.6 g-mol) of sodium pyrosulfite and 168 g of a 25% solution of ammonium hydroxide was carried out in the same manner as described in Example 1 by adding 1.330 g of an aqueous solution of the sodium and ammonium double salt of acylamidoethylene sulfosuccinic acid having the formula: That is, OO 01Na, where R is Oe -Clf, and the content of the target product is 32% by volume. The average molecular weight of the product thus obtained was 5
37. Total solids 40.8%, degree of conversion (desired product/initial amide') e to %, solubility in 0014 4.
9%, viscosity at 20°C 22.0 mPag, density a,
1. tozkg/♂, pH (10% solution') 6.11
It is 5.

Example 6 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1.

In a 500 ml flask equipped with a stirrer, distillation apparatus and thermometer, add distilled fatty acid methyl ester (Fraction III) 2
99 g (1,00 g-mol) and 20 g (0,3271-mol) of monoethanolamine were added, and the treatment was carried out in the same manner as described in Example 1 above. Then fatty acid methyl ester busy monoethanolamine @OK
<141 gg-mol) and 8.2 g of a 37.8% monoethanolamine solution of sodium 2-amine ethoxylade are added and stirred for 1.5 hours at a temperature of 90 °C. Methanol and excess monoethanolamine are distilled off as in Example 1.

330 g of fatty acid monoethanolamide with an average molecular weight of 328 are thus obtained. The product yield, calculated on the degree of conversion of monoethanolamine, is equal to 95.5% of theory.

The resulting fatty acid monoethanolamide 328 g K maleic anhydride 121.4 g (1,23
8 g-mol) and stirred for 2 hours at this temperature to produce 449 g of acidic mannic acid monoethanolamide (MaL/Iak acylamide ethylene). Sulfidation and neutralization of acidic maleic acid monoethanolamide
9TOml of water, 15ml of potassium pyrosulfite at a temperature of 90°C
Similar to the method described in Example 1, by adding it into a solution containing 8.3 g (0,712 g-mol) and 149.5 g (1,424 g-mol) of jetanolamine. Do it in this way. 1.72Of aqueous solution of jetanolamine and potassium double salt of acylamide ethylene sulfosuccinic acid having the following general formula is obtained. That is, spirit SO,
．． 3% by volume. The average molecular weight of the target product thus obtained was 649, total solids 41.4%, degree of conversion (target product/initial amide) SO, S%, solubility in 001 a 4.2%, 20°C. Viscosity at 20.0 IIPI
L! 10, Density (1,1,089 kg/rn', p
H (10% solution) 7.05.

Example T The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1.

91,000m1 equipped with stirrer, distillation equipment and thermometer
1610 g of jetanolamine (1,0 g-
mol), 31 of sodium 2-amine ethoxylade
．． Add 8.0 g of 8% monoethanolamine solution. 295 g (1,00 g−
mol) and stirred for 2 hours at a temperature of 80°C.

The mixture is heated to a temperature of 90° C. under a reduced pressure of 200 mmHg and the methanol is distilled off to produce 428 g of fatty acid jetanolamine with an average molecular weight of 424. The product yield, calculated on the degree of conversion of diptanolamine, is 88% of theory.

To 424 g of fatty acid jetanolamine thus produced, 127.5 g (1,30 g-mol
) of maleic anhydride and stirred at this temperature for 3 hours to obtain 551 g of acidic maleic acid dibutanolamide [maleic acylamide-N-(1-methyl,2-hydroxy)-propyl-H-(1,2 -dimethyl)ethylene].

Sulfurization and neutralization of acidic dibucturamide maleate is carried out in a solution consisting of 1,500 ml of water, 142 g (0,747 g-mol) of sodium pyrosulfite and 222 g (1,4 gg-mol) of triethanolamine at a temperature of 10°C. Proceeding as described in Example 1 by adding it, an acylamide-N-(1
-methyl,2-hydroxy)propyl-N-(1,2-
2,412 g of an aqueous solution of the triethanolamine and natrinoum double salt of dimethyl)-ethylene sulfosuccinic acid are produced. That is, (3H1OH, where R is Go-Ot*, the content of the target product is 24.1
It is capacity %.

The average molecular weight of the target product is 174, total solids 36.2%
, degree of conversion (desired product/initial amide) 74.8%, 0
Solubility in 01a 7.2%, viscosity at 20°C 28 m
Pa5. , density d41.062 kg/ni", pH (
10% solution) 6.95.

Example 8 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1.

500 ml flask equipped with stirrer, distillation apparatus and thermometer 1 CN-ethylethanolamine 116 g (1,
30 g-mol), 7.2 g of a 37.8% monoethanolamine solution of sodium 2-amine ethoxylade
295 g (1,0 Og) of distilled fatty acid methyl ester (Fraction ■) pretreated with
-mol) and stirred at a temperature of 80°C for 1.5 hours. The methanol is distilled off at a temperature of 90° C. under a reduced pressure of 200 mmHg. The extra ethylethanolamine is 1
Distillation is carried out at a temperature of 120-125° C. under reduced pressure of 0-15 mmHg to produce 355 g of fatty acid N-ethylethanolamide with an average molecular weight of 352. The product yield calculated for the degree of conversion of N-ethylethanolamide is 95% of theory.

108 g (1.10 g-mol) of maleic anhydride is added to 352 g of fatty acid H-ethylethanolamide at a temperature of 90° C. and stirred at this temperature for 2 hours to produce 460 g of acidic maleic acid ethylethanolamide. Sulfurization and neutralization of acidic ethyl maleate ethanolamide at a temperature of 70 ° C containing 1.400 ml of water, 120 g (0,63 g-mol) of sodium pyrosulfate and 77 g (1,26 g-mol) of monoethanolamine. By adding it to a solution of Aqueous solution 2
．． 052g is produced. That is, CH1(3Hs 80 @M!L where R is C'1g-011 and the content of the target product is 24
．． 3% by volume.

The average molecular weight of the target product is 614, total solids 31.2%
, degree of conversion (desired product/initial amide) 81.6%4
Solubility in CGL 5.9%, viscosity at 20°C 310 m
Pag, density d, 1.086 kg/m”, pH (1
0% solution) 7.02.

Example 9 The synthesis of fatty acid methyl esters is carried out in a manner similar to that described in Example 1.

295 g (1,011-mol) of distilled fatty acid methyl ester (fraction ■) and 15 g (0,246 g
-mol) of monoethanolamine is added, and the subsequent treatment is carried out in the same manner as described in Example 1 above.

80g (1,310g-a+ol)tDmo/xl/
-lamine is added to the fatty acid methyl ester, the mixture is stirred at a temperature of 80 DEG C. and then 5.6 g of the catalyst solution, namely a 28% methanol solution of sodium methanolade, are added. Reaction time is 1.2 hours.

Methanol and excess monoethanolamine are removed as described in Example 1.

In this way, 325 g of fatty acid monoethanolamide with an average molecular weight of 324 is obtained. The product yield, calculated on the degree of conversion of monoethanolamine, is 95.6% of theory. The further work-up of the process is carried out according to the procedure described in Example 1 to produce the desired product similar to that of Example 1 above.

The quality and properties of the compounds prepared as described in Examples 1-9 are shown in Tables 1-3.

Example 10 A foaming solvent for bath contains the following components (% by volume). That is, the quality characteristics of triethanolamine and sodium double salt of acylamidoethylene sulfosuccinic acid 32 fragrance 1.5 water balance whipping solvent are shown in Table 4 below.

Example 11 The infant hair wash contains the following ingredients (% by volume).

i.e. Acylamide ethylene sulfosuccinic acid triethanolamine and sodium Mu double salt 5 Fragrance 0.1 water remainder The quality characteristics of the infant hair wash are shown in Table 4Ilc below.

Example 12 The hair wash contains the following ingredients (% by volume).

That is, triethanolamine and sodium double salt of acylamide ethylene sulfosuccinic acid 20 (3
-Ou fatty acid jetanolamide 3.5 Ethanol 1.5 Sodium chloride 2.0 Fragrance 1.0 Water Balance The quality characteristics of the hair wash are shown in Table 4 below.

Example 13 The hair wash composition contains the following components (% by volume).

That is, triethanolamine and sodium double salt of acylamide ethylene sulfosuccinic acid 12 a, -ai fatty acid jetanolamide 3.0 Ethanol 0.75 Sodium chloride 3.5 Fragrance 0.15 Water Balance quality characteristics of the hair wash It is shown in Table 4 below.

Continued from page 1 ■ Int, CI, ' Identification symbol 0 Inventor Avuo Artourović Ukivii 0 Inventor Avuo Irmalović Poom 0 Inventor Oskar Peeterović Kouri 0 Inventor Hellier Petrovna Urbele o Inventor Aμ Alfredović Asi0 Inventor Aμ Vordemarovich Piarun @ Applicant Oporonopokazacerny Riibolovets Leather-Kolkhozymeni Varnish/Process p M + -re H? Unai Serial Number Soviet Union, Tarif, Uliitsa Rosiaputie, Russian Soviet Union, Tarif, Fourvear Shipuruuse, 20th Caveis Soviet Union, Valusky Lion, Nis/Sviiumushi, Uliitsa Cal 9 Teie 8, Cavi 21 Soviet Union, Tarif, Uliitsa Musta MIIAETIE, 82 KEVY 136 Soviet Union, VALUSKY LION, NIS/SVI IMPLANT, URIITSUA CARU 9 TAIE 2, KEVY 10 Soviet Union, Tarif, URIITSUA IDI VILDE TEIE, 10 & KEVY 17 Soviet Union, VALUSKY LION, NIS/SVI VILDE (No address) Procedural amendment (spontaneous) March 9, 1980 Director-General of the Patent Office Kazuo Wakasugi 1, Indication of the case 1981 Patent application, page 24, No. 12
Relationship to Case No. Patent Applicant Address Noviyet Federation, Tarino, Uriitsa Academia Teie, 15 Name Instituto Hi ξ−
Academy - Nakku soldiers - 4 - Estonskoy Nisnis 7 - 61 people 4, agent 5, amendment order 8 (=I Showa year, month, day, content of amendment ← Patent application No. 58-245612) 1, Specification S No. 9 In the γth line, "Hydrogen CH3J [hydrogen.

-Correct as CH, J.

2. On the 9th line of the same page, “R3ke-CH,-Cl, J [
R8 is corrected as CH2CHt + J.

3 BA detailed oath No. 10, No. 13 r-cot ion”.

4 r5.35 town-equima/ on page 11, line 13
Correct g J to r 5.3 5 B-equiv/lJ.

5-1"I, page 16, line 13, [N-methylethanol] is corrected to "N-methylethanolamine."

6 In the same page, page 22, line 9, [Freezing point -9.3°CJ is corrected to "Freezing point 9.3°CJ.

7. "15" from page 23, line 20 to page 24, line 1
Corrected to 11 o'clock MJkrL5 o'clock J.

8. On page 36, line 20, "dibutynolamine" is corrected to "dibutanolamine."

9 Same page 38, line 0 I am corrected.

1 (1. Same negative line 11 r RuCra Cto J
l-R is corrected as ell-CroJ.

11, page 38, line 14, is corrected to read "ethylethanolamine" t-rN-ethylethanolamine.

12, page 40, lines 3-4 and lines 4-5, ``Acidic maleic acid ethylethanolamide Jkr Acidic maleic acid N-ethylethanolamide J'' is corrected.

13 Correct the sentence ``Sodium pyrosulfate'' in line 6 of Dosei to read ``Total 1-sodium pyrosulfite''.

14, row 14 of Table 1 on page 45 of the same I am corrected.

15. In the second line of Table 2 for Allotropy 46jr, "Azyla-do-alkylene-succinic acid or fc is (Correct J to [acyla-do-alkylene (or)".

16 Line 11 of Table 2 (D r 6 R1 = C
rt Ct+ Jt r 6 R+ − Crt −
Correct Ctt J.

11, Table 2, row 12 1ii'f) r T Cto
Correct as Crt Jkrr C1l CreJ.

18. In the second line of Table 3 on page 41, "azila-do-alkylene or (") is corrected to "azila-do-alkylene (or)."

1, 9. rEfJ table 11t line 49 (D r 4 R
1 = C1s-CH=-CJ(sJYt r 4 R
1 = Cr. s- On , Re = -CHsJ and t
tr right t le.

Claims (8)

[Claims] (1) The following general formula, (where R1 is Go-(3t+ straight chain hydrocarbon group R2 is hydrogen -〇H□-CH*OHs, -OH containing -OHfi
Oh. -OH, -0H-OH OH. R,,R,,R・represents each hydrogen and (t or)-CM t
-OHs -OH; M6 is a Hat, and an amine and alkali metal double salt of acylamidoalkylene (or acylamido-N-hydroxyalkyl-H-alkylene) sulfosuccinic acid. (2) Acid value 5 G mg KOH/g or less, saponification value 1
81-192n1gKOH/g, bromine number 60-70n
@Br/100g of fatty acid and glyceride fatty waste originating from a seafood processing plant is heated under reflux and treated with methanol in the presence of sulfuric acid to produce a reaction mixture y, from which a fat consisting of glyceride and fatty acid methyl ester is produced. separating the layers and treating with methanol in the presence of sulfuric acid at a temperature of 50-60°C to produce the reactants;
From this, the anhydrous fat layer is separated and treated with methanol in the presence of an alkali at the boiling temperature of methanol to produce a reaction mixture containing fatty acid methyl esters, and the fatty acid methyl esters are separated and treated with alkali metals at a temperature of 70-90°C. or their amides or their alcoholades, in the presence of a catalyst selected from the group consisting of: The fatty acid alkylolamide is treated with maleic anhydride at a temperature of 60-90°C to produce a maleate salt of the fatty acid alkylolamide, and then the maleate is treated with pyrosulfite at a temperature of 60-90°C in an aqueous medium. Acylamide alkylene (or acylamido-N-hydroxyalkyl-N - A method for producing amine and alkali metal double salts of sulfosuccinic acid (alkylene). (3) In order to improve the quality of the desired product, the fatty acid methyl ester is mixed with 5-10% by volume of the fatty acid methyl ester at a temperature of 10-80°C before the above treatment with the alkylolamine in the presence of the above-mentioned catalyst. The method according to claim 2, characterized in that the waste alkylolamine is removed after pretreatment with the alkylolamine collected at a value of . (4) As the alkylolamine, monoethanolamine, jetanolamine, diisopropanolamine,
The method according to claim 2 or 3, characterized in that N-methylethanolamine, N-ethylethanolamine, jetanolamine is used. (5) Sodium 2 was used as a catalyst to simplify the method.
5. The method according to any one of claims 2 to 4, characterized in that - aminoethoxylate is used. (6) Claim 2 characterized in that monoethanolamine, jetanolamine and/or triethanolamine is used as the ethanolamine.
5. The method according to any one of items 5 to 5. (7) Surfactant, i.e. acylamidoethylene sulfosuccinic acid of triethanolamine and sodium sulfosuccinic acid of the following formula: It consists of salt, fragrance and water, and the above ingredients are in the following proportions (% by volume): triethanolamine and sodium double salt of acylamide ethylene sulfosuccinic acid 5.0-32.0 fragrance 0.1-1 .5 A cleaning agent characterized in that water is present in the balance. (8) 0s-Ou fatty acid jetanolamide, sodium chloride and ethanol in the following component ratio (volume %)
, triethanolamine and sodium cypress salt of acylamide ethylene sulfosuccinic acid 12.
0-20.0 C・-071 fatty acid jetanolamide 0.5-3.
Claim 7 additionally contains: 5 sodium chloride 1.0-3.5 ethanol 0.3-1.5 fragrance 0.1-1.5 water balance Cleaning agents listed in .